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Water → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-isopropenyloxycarbonyl-L-valinamide

HRID 1900171
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1900171
CN1CCOCC1.Cl[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].Cl.[C:16]([C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][CH:24]([NH:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:32])[CH3:31])[NH2:29])[CH3:25])=[CH:20][CH:19]=1)#[N:17].O>C(Cl)Cl>[C:16]([C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH:24]([NH:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:31])[CH3:32])[NH:29][C:9]([O:11][C:12]([CH3:14])=[CH2:13])=[O:10])[CH3:25])=[CH:34][CH:35]=1)#[N:17]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 79724-MethylmorpholineHCID 22866849N1-[2-(4-cyanophenoxy)-1-methylethyl]L-valinamide hydrochloride

Produkt 1

HCID 54557867N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-isopropenyloxycarbonyl-L-valinamideAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.6 g of N-methylmorpholine, and subsequently 0.4 g of isopropyl chloroformate were added to a solution containing 0.9 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]L-valinamide hydrochloride dissolved in 50 ml of methylene chloride at -15° C. The mixture was allowed to sit and warm naturally to room temperature and stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the dichloromethane layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and then the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 0.23 g of the desired product in the form of colorless grains (yield: 13% ).

Aufarbeitung

  1. washAfter the dichloromethane layer was washed with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customthe methylene chloride was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-84bb9bd545154f11a97a30c5967bd9d5
Quelldatensatz
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05574064

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